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Thanks for the input... I was looking at the Nikon Monarch 5 in 8x42.
He is retired and has a deer feeder set up around 150 yards from his sitting chair. These days he just likes watching the deer, hogs, and yotes come through the pasture early in the morning and in the evenings. He's not scaling Mount Everest or going on safari in Africa, so ruggedness isn't my prime concern. Just want to make sure he's got clear glass that draws in a ton of light as his eyes get worse.
Besides his eyes getting worse, one also has to consider the ability to hold a large bino steady. This first suggestion is no longer produced, but can still occasionally be found on internet sites/ebay. The Leupold Hawthorne 7x42 can sometimes be found in your price range. It is a superbly sharp bino, and in fact is sharper in the central area that others that cost twice as much. A 7x is easier to hold steady, and the 6mm exit pupil makes it very forgiving when it comes to eye placement. It also has lots of eye relief, which is important as he probably wears eyeglasses, or will be soon. Another nice thing about them is that they are not quite as long as many other 42mm binos. They also come with a very comfortable neckstrap. If you are considering an 8x42, then this 7x42 will do everything that an 8x will do, and this particular bino will do everything better than any other 8x bino in your price range. The only possible hitch is finding one when you want one.
If you can't find a Hawthorne, then consider the Vanguard Endeavor ED 8x42. You can get them for about $249, and there is currently a $50 rebate until the end of the year. This makes it cheaper than the M5. It is a very solid choice for your situation. It's focus wheel is better than the Diamondback, and it has a wider FOV than the M5. Also has one of the better neckstrap/case combo in this price range. I think it's eye relief is over 17mm, which would make it suitable for eyeglass use. Check on that to be sure. These are sharp and bright, and have as solid a build as any other in it's price range. I would certainly go for this one over a Nikon M5, even if they were the same price.
The 8x42 M5 is a solid choice, but be aware that it has a very narrow FOV. Now, if he isn't used to using a bino, then he won't know what he is missing. However, I know I could not ever live with such a narrow FOV. Heck - I've got 10x binos that have a wider FOV than this one has. But it does have a nicely sharp view, and a very good focus wheel and comfortable grip. If he served in the navy aboard ship, then he might like this one (you know - looking at the world through a port-hole...).
Lastly - the Bushnell Ultra Legend HD 8x36 is a decent little bino with a smaller footprint than the 42mm binos. Decently sharp and bright, and a good focus wheel with little backlash. I don't know if it has enough eye relief, but you can check that for yourself. It's a nice little bino that can often be found under $229. Be aware however that the diopter adjustment ring on the right ocular has to be unlocked to use, and it will break easily if you try to move it when locked.
